NP-MRD: Showing NP-Card for (1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol (NP0175875)

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Record Information

Version

2.0

Created at

2022-09-03 13:26:47 UTC

Updated at

2022-09-03 13:26:47 UTC

NP-MRD ID

NP0175875

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol

Description

Penitrem C belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol is found in Penicillium crustosum and Penicillium solitum. Based on a literature review very few articles have been published on Penitrem C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032215262D          

 43 51  0  0  1  0            999 V2000
   -1.8584    1.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360    1.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    0.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1318    0.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455   -0.2610    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9094   -0.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5368    0.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053    0.3132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6991    1.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6089    1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2538    2.3017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5686    2.3666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  3  4  1  0  0  0  0
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  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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  8 12  1  0  0  0  0
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 40 42  1  0  0  0  0
 10 42  1  0  0  0  0
 23 42  1  0  0  0  0
 42 43  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309032215262D          

 43 51  0  0  1  0            999 V2000
   -1.8584    1.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0360    1.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1416    0.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1318    0.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455   -0.2610    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9094   -0.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5368    0.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053    0.3132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6991    1.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1312    1.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3866    1.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6089    1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2538    2.3017    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5686    2.3666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2483    3.3549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5293    3.0794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2740    3.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7383    4.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7414    4.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0516    3.1590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4067    2.4143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2314    2.3926    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7994    2.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6016    2.7983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8358    2.0073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4038    2.6056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6380    1.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2060    2.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0081    2.2203    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5761    2.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2424    1.4292    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0445    1.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6125    1.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2788    0.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6744    0.8308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8722    1.0235    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3042    0.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5021    0.6178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2678    1.4089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6999    0.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4657    1.6016    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3709    0.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  2  0  0  0  0
  4 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 17 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 11  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 32 36  1  0  0  0  0
 37 36  1  1  0  0  0
 28 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 26 40  1  0  0  0  0
 40 41  1  1  0  0  0
 40 42  1  0  0  0  0
 10 42  1  0  0  0  0
 23 42  1  0  0  0  0
 42 43  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0175875

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H]1O[C@H]2CC[C@]3(C)[C@]4(C)[C@@H](CC[C@@]3(O)C2=C[C@H]1O)[C@@H]1OC(C)(C)[C@H]2C[C@H]3[C@@H]2C2=C5C(NC4=C15)=CC(Cl)=C2CC3=C

> <INCHI_IDENTIFIER>
InChI=1S/C37H44ClNO4/c1-16(2)31-25(40)14-21-26(42-31)9-10-35(6)36(7)20(8-11-37(21,35)41)32-30-29-24(39-33(30)36)15-23(38)19-12-17(3)18-13-22(27(18)28(19)29)34(4,5)43-32/h14-15,18,20,22,25-27,31-32,39-41H,1,3,8-13H2,2,4-7H3/t18-,20+,22+,25-,26+,27+,31-,32+,35-,36-,37-/m1/s1

> <INCHI_KEY>
BVVRIERIEDMORG-UWOVGSIKSA-N

> <FORMULA>
C37H44ClNO4

> <MOLECULAR_WEIGHT>
602.21

> <EXACT_MASS>
601.2958866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
69.99330835285318

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,8R,9R,11S,14R,15S,24S,26S,27S)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0^{2,15}.0^{5,14}.0^{6,11}.0^{16,30}.0^{18,29}.0^{21,28}.0^{24,27}]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol

> <ALOGPS_LOGP>
5.74

> <JCHEM_LOGP>
5.715745096000002

> <ALOGPS_LOGS>
-6.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.027413250915632

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.42088155941217

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3536229414882666

> <JCHEM_POLAR_SURFACE_AREA>
74.71000000000001

> <JCHEM_REFRACTIVITY>
169.37240000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.62e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,8R,9R,11S,14R,15S,24S,26S,27S)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0^{2,15}.0^{5,14}.0^{6,11}.0^{16,30}.0^{18,29}.0^{21,28}.0^{24,27}]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.469   3.270   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.934   3.149   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.271   1.758   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.264   1.637   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.246   0.392   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0      -1.018  -0.487   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       1.698  -0.122   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.869   0.878   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       4.303   0.585   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       5.038   1.938   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.978   3.055   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.588   2.392   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.137   2.907   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.474   4.297   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.061   4.418   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.464   6.262   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.988   5.748   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.378   6.411   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.378   7.582   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.251   7.680   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.830   5.897   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.493   4.507   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.032   4.466   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.092   5.583   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.590   5.224   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.027   3.747   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.087   4.864   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      10.524   3.387   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.584   4.504   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.082   4.144   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.142   5.261   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.519   2.668   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.016   2.308   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.077   3.425   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.454   0.832   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.459   1.551   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      10.961   1.911   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.901   0.794   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.404   1.153   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.967   2.630   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.906   1.513   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.469   2.990   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       6.292   1.460   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   42                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11    8   13                                                  
CONECT   13   12    4   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   14   18                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   11   23                                                  
CONECT   23   22   24   42                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   40                                             
CONECT   27   26                                                            
CONECT   28   26   29   37                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   36                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   32   37                                                       
CONECT   37   36   28   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   26   41   42                                             
CONECT   41   40                                                            
CONECT   42   40   10   23   43                                             
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₄₄ClNO₄

Average Mass

602.2100 Da

Monoisotopic Mass

601.29589 Da

IUPAC Name

(1S,2R,5S,8R,9R,11S,14R,15S,24S,26S,27S)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0^{2,15}.0^{5,14}.0^{6,11}.0^{16,30}.0^{18,29}.0^{21,28}.0^{24,27}]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H]1O[C@H]2CC[C@]3(C)[C@]4(C)[C@@H](CC[C@@]3(O)C2=C[C@H]1O)[C@@H]1OC(C)(C)[C@H]2C[C@H]3[C@@H]2C2=C5C(NC4=C15)=CC(Cl)=C2CC3=C

InChI Identifier

InChI=1S/C37H44ClNO4/c1-16(2)31-25(40)14-21-26(42-31)9-10-35(6)36(7)20(8-11-37(21,35)41)32-30-29-24(39-33(30)36)15-23(38)19-12-17(3)18-13-22(27(18)28(19)29)34(4,5)43-32/h14-15,18,20,22,25-27,31-32,39-41H,1,3,8-13H2,2,4-7H3/t18-,20+,22+,25-,26+,27+,31-,32+,35-,36-,37-/m1/s1

InChI Key

BVVRIERIEDMORG-UWOVGSIKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium crustosum	LOTUS Database	35616633
Penicillium solitum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Tetralin
3-alkylindole
Indole
Indole or derivatives
Aryl chloride
Aryl halide
Pyran
Benzenoid
Tertiary alcohol
Pyrrole
Heteroaromatic compound
Cyclic alcohol
Secondary alcohol
Azacycle
Oxacycle
Dialkyl ether
Ether
Alcohol
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.74	ALOGPS
logP	5.72	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	74.71 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	169.37 m³·mol⁻¹	ChemAxon
Polarizability	69.99 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023571

Chemspider ID

31115353

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76316105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

MOL for NP0175875 ((1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol)

3D MOL for NP0175875 ((1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol)

3D SDF for NP0175875 ((1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol)

3D-SDF for NP0175875 ((1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol)

PDB for NP0175875 ((1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol)

3D PDB for NP0175875 ((1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol)

SMILES for NP0175875 ((1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol)

INCHI for NP0175875 ((1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol)

Structure for NP0175875 ((1s,2r,5s,8r,9r,11s,14r,15s,24s,26s,27s)-20-chloro-14,15,32,32-tetramethyl-23-methylidene-9-(prop-1-en-2-yl)-10,31-dioxa-17-azanonacyclo[24.4.2.0²,¹⁵.0⁵,¹⁴.0⁶,¹¹.0¹⁶,³⁰.0¹⁸,²⁹.0²¹,²⁸.0²⁴,²⁷]dotriaconta-6,16(30),18,20,28-pentaene-5,8-diol)